


Because of a Bet

by plant_boy



Category: Supernatural
Genre: Bisexual Dean Winchester, Bottom Dean Winchester, Boys in Skirts, Castiel Loves Dean Winchester, Dean Winchester Has a Panty Kink, Dean Winchester Loves Castiel, Dean Winchester Wears Panties, Dean Winchester Wears a Skirt, Dom/sub Undertones, Good Sibling Sam Winchester, Happy Ending, Lost a Bet, M/M, Panty Kink, Plot What Plot/Porn Without Plot, Praise Kink, Resolved Sexual Tension, Sexual Tension, Shameless Smut, Smut, Top Castiel (Supernatural), Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2020-12-22
Updated: 2020-12-22
Packaged: 2021-03-10 19:47:03
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,368
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28232643
Author URL: https://archiveofourown.org/users/plant_boy/pseuds/plant_boy
Summary: dean and sam made a bet about what kind of monster they were hunting. dean bet vamps, sam bet werewolves. dean lost. sam made dean wear a skirt for a day around the bunker. cas likes it a little too much. smut ensues. enjoy :)
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester, Destiel
Comments: 3
Kudos: 151





	Because of a Bet

“I’m telling you Sammy-it’s vamps.” said Dean, very self assuredly. “Dean-it’s clearly werewolves, look at all of the signs.” said Sam with a sigh. “Yeah, you wanna bet?” asked Dean cockily. Sam sighed and shook his head. “You know what, sure. If its vamps-you win, if its werewolves-I win.” Dean grinned and stuck out his hand. “Deal.”

It was werewolves. 

“Alright, give it to me. You won, what do you want?” Sam grinned, although a bit disappointed that Dean remembered because he couldn’t surprise him. “On the way back to the bunker, we’re going to stop at a mall...and buy a skirt. And tomorrow, you’re going to wear it for the whole day.” Sam finished, smirking. “But...but a bunch of the other hunters-and Cas are at the bunker.” Dean spluttered. “Exactly.” Sam grinned. 

They stopped at a mall on their way back from the hunt. Sam made Dean try on a bunch of skirts, and made sure the one he picked fit him properly so he couldn’t back out at the last minute. It was a black mini-skirt, because of-fucking-course it was.

When they got back to the bunker Dean immediately went back to his room and stayed there the whole night. 

-

Dean woke up with his alarm. He groaned and rolled over in bed. He wiped the sleep from his eyes, and his eyes shot open when he remembered the events of yesterday. He groaned again and buried his face in his pillow. 

“No, you know what, I’m not gonna give Sammy the satisfaction.” Dean told himself. Dean reached into his drawer and pulled out his favorite pair of pink satin panties. Rhonda Hurley had truly changed his life, bless that woman. Next, he put on the skirt that they'd bought yesterday, it really was a pretty one. He found a tight black t-shirt that was the same shade as the skirt and put it on. He brushed his teeth and ran his hands through his hair. He looked good and he knew it. He was ready to face the day. Or so he thought. 

Thankfully there was no one in the kitchen when Dean went to get his necessary daily caffeine. He drank his coffee in peace, grateful that he was alone, and let the energy pass through his body. 

Then Sam walked in. 

He wolf whistled. “Looking good, Dean.” Sam grinned, trying to suppress a giggle. Dean did a very exaggerated curtsy. “Take it all in, little brother, I look good.” Dean said, feeling more confident. And then came Cas. “Morning, buddy.” said Dean, trying to pretend like everything was normal. Cas froze. His eyes roamed all over Deans body for longer than would be considered normal. Cas coughed. “Uh-good-good morning Dean.” Sam attempted to suppress a giggle. “Hey Cas, doesn’t Dean look good today?” asked Sam, trying to push Cas’ buttons. “Um-yes-very much so. Excuse me.” Cas coughed and practically ran out of the room. Dean was oblivious, and simply drank his coffee and shook his head. “Frickin' angels, man.”

“Dude, your head is so far up your ass it's saying hello to your lungs.” Said Sam, completely exasperated. “What the fuck is that supposed to mean?” asked Dean. Sam just shook his head and left the room. “Huh.” said Dean as he sat down at the table in the kitchen. 

“Could it be? Could Cas feel the same? Does he like how I look in this?” Dean thought to himself. Then he had an idea. If he was right, he had nothing to lose. 

He left the kitchen and saw that Cas wasn’t in his room, so he would probably be in the main common area. He passed some of the other hunters on his way over there and they all grinned at him. He grinned back. 

“Hey Cas,” Dean said hesitantly as he walked into the room. Cas immediately shot up from his spot at the map table. “Dean.” he said, his voice deeper than usual. “Whatcha doing, buddy?” Dean asked. “Just-just reading.” said Cas, picking up his book to show Dean. Cas’ hands were shaking as he tried to restrain himself from jumping Dean right then and there. And then he dropped the book. Just as Dean had planned. 

“Here, let me grab that for you.” said Dean. And then he turned around and picked up the book, revealing his ass in the pink panties. He heard Cas gasp and try to muffle it as a cough. “Here you go.” said Dean, as he handed Cas his book back. Dean then grinned and winked and walked away, purposely strutting to make his ass look good. Cas’ knuckles turned white as he gripped the book. 

Dean was walking back to his room, but the next thing he knew, he was in his room and being slammed up against the door. “Are you purposely trying to antagonize me?” growled Cas. “M-maybe.” mumbled Dean, trying to maintain eye contact without blushing. Cas stared at him, his pupils wide. Dean didn’t know if he started it or if Cas did, but they were kissing. He was kissing Cas. Cas was kissing him.

It was rough and desperate and it was everything. Cas had his knee in between Dean’s legs and Dean was using it to rut his hard cock against. Cas has his hands all up in Dean’s hair and Dean was loving every second of it. “B-bed.” Stuttered out Dean as soon as he had a breath. 

Cas pulled him away from the door and kissed Dean as he pushed him onto the bed. Dean failed to hold back a moan as the angel pushed him down. He liked being manhandled, sue him. Cas pulled off Dean’s shirt, revealing his tattoo and miles of beautiful skin. He began to bite and suck marks all over. “Mine.” growled Cas. “Shit-yours, Cas.” Dean said, as he tilted his neck to the side to give Cas more access to his skin. He loved being marked. He loved the possessive side to Cas. 

Finally, Cas lifted up Dean's skirt to reveal his hard cock trapped in the panties, a huge wet spot spreading from his pre-cum. Cas didn't even try to stifle his gasp as he stared at the beautiful sight before him. “I love you like this.” Cas whispered, his eyes dark with lust. Dean just moaned in response. He sucked on Deans cock through the panties, and Dean moaned even louder, the feeling was unreal. 

Cas moved the panties down slightly, and Dean's cock sprang out, leaving pre-cum on his stomach. Cas sucked hard on the head and Dean almost came from just that. “Fuck, Cas.” Dean managed to get out. “I’m not done with you, yet.” Said Cas. Dean loved that Cas was in control. Cas flipped Dean over so he was on his stomach. Dean had his ass in the air almost immediately, he could be embarrassed later, but now he couldn't care less. 

Cas flipped the skirt up, revealing Dean's perfect ass, the panties barely covering anything. He ran his hands over Dean, and gave a tentative smack. Dean moaned loudly, shocked himself. Cas grinned to himself. “You’d look so pretty with my hand print on your ass.” said Cas, leaning over to whisper in Dean's ear. “Yesss...Cas.” Dean replied. Cas continued to slap Dean on the ass, admiring his handiwork (hahah pun intended). He kissed over the mark his hand had left, and the red glowed. 

He pushed the panties to the side again, but didn’t dare take them off. He loved how they looked on Dean. “So pretty for me.” Cas murmured, as he ran his calloused fingers over Deans taint and rim, just brushing against it. Dean bucked his hips at the feeling. “So desperate for me.” Cas tsked. “Fuck-please-please Cas.” Dean begged, rubbing himself against the bed, desperate for some friction. “Hmm...what was that?” asked Cas, teasing. “Please Cas-Castiel.” said Dean loudly, and more clearly. 

“Please what, boy?” Cas growled into his ear. Dean moaned. “Please fuck me, Cas. I need you.” Dean begged. “Good boy.” said Cas, smiling to himself. “Where do you keep your lube, baby boy?” asked Cas. Dean moved his arm to point to the drawer beside him. Cas pulled it open and smirked as he saw Dean's collection of panties. He couldn't wait to see Dean wear all of them. He poured the lube over his fingers and rubbed his thumb over Dean's hole, trying to elicit a reaction from him. 

Cas slipped his finger into Dean's hole, and it went in with ease. “How does that feel?” he asked Dean. “More...please.” Dean asked, shoving his ass up in the air more, trying to get Cas to give him another finger. “What a good boy you're being for me, Dean.” Cas praised, pleased with Dean. he added another finger. “Yes-I wanna be good for you.” Dean said, moaning as Cas circled his fingers around inside him. 

“Think you can take another one, hmm?” asked Cas, fully enraptured at how well Dean was taking him. “Yes, Cas, please, come on, I can take it.” said Dean, who couldn't wait for more. He wanted all of Cas. He would take whatever Cas would give him. Cas poured more lube on his hands and added a third finger. Dean moaned and began fucking himself on Cas’ fingers, trying to show Cas that he was ready.

“Fuck, just look at you, taking my fingers so well.” said Cas. Dean glowed under the praise. He loved hearing Cas swear. He knew the angel was just as wrecked as he was when he started to swear. Cas admired Dean for a few more moments, seeing how well the man took his fingers, desperate for more, and so close to the edge. “Come on, Cas.” Dean whined, more desperate by the moment. 

“You want my cock, don’t you, huh, Dean?” whispered Cas in Dean’s ear. Dean's eyes popped open, shocked at how forward Cas was being, but loving every second of it. “Yes please Cas, I’m ready-please fuck me.” Dean practically begged. “Good boy, asking so nicely. And I'm going to give it to you. You’re going to take it so well, aren’t you?” Cas asked. Dean moaned, Cas’ fingers hitting his prostate at that second. “Yes-Cas-I’ll take it so well, wanna be good for you.” 

Cas rubbed his cock through his pants. It was painfully hard and begging for attention. How could it not be after seeing Dean in this state for such a long time, it's a wonder he could hold out this long. Cas groaned at the friction. Dean immediately swiveled his head at the sound. “Wanna taste you, Cas.” Dean managed to get out, while Cas’ fingers were still inside of Dean, and touching himself. “Yes, Dean.” Cas said, his head tilted back at the small amount of friction he was giving himself. 

Cas slowly removed his fingers from Dean, much to Dean’s disappointment. The disappointment faded very quickly as Cas opened his pants and Dean came face to face with Cas’ cock. Fuck. That was hot. Dean licked the pre-cum from the head, and relished the low noises Cas was making. Dean had barely begun to suck when Cas was pulling him off. Cas pulled him into a deep kiss that they both got lost in. It soon got heated and they pulled apart. 

They were both breathing heavily as Cas reached for the lube. Dean was still worshiping Cas’ chest and neck, as he covered them with his kisses and bites. Cas lubed up his cock and listened as Dean's heartbeat increased. Cas pulled Dean into another kiss and they slowly ended up back to lying down on the mattress. “I’m ready, Cas.” Dean said, his voice quiet but very sure. 

Of his own accord, Dean turned back to lying on his stomach, unknowingly sticking his ass back in the air. He felt Cas push the tip of his cock against his rim, and they both moaned as Cas bottomed out. “Good boy, Dean, taking me so well.” Cas murmured, truly in awe of how well Dean was taking him, as though their bodies were made for each other. As they both accustomed themselves to this new situation, Cas began to move. 

Cas’ thrusts started slowly, he was still worried that he was hurting Dean. Oh, but when Dean started fucking back, Cas really started. He thrusted hard, and Dean moaned loudly. Cas kept up his pace, hard and fast and rough, and it was perfect for them. They were so on edge and had been for such a long time, they would take their time with each other later. Cas gripped Deans panties for leverage and kept going faster. The panties kept their tight grasp on Deans cock and it was almost too much. 

“Cas...I’m so close...I wanna come...please.” Dean begged, his voice rough and cracking, he could barely form the sentence, pleasure coursing through him. “Come for me, Dean.” Cas growled in his ear with a particularly hard thrust against his prostate, and Dean came so hard, seeing stars. Cas felt Dean clenching around him and hearing all of the beautiful noises Dean was making, and he came hard inside of Dean. He moaned deep and low. 

It felt amazing. He pulled out slowly, and Dean missed the feeling of being filled. “You look so beautiful with my cum dripping out of you.” said Cas, his voice gravelly post-orgasm. If Dean hadn't just came, he would've gotten hard again just hearing that. Dean was still floating and didn't notice Cas cleaning both of them off. When Cas came back into bed, he pulled Dean close to him, making Dean the little spoon. Dean was a cuddler, sue him

Dean didn't want to ruin the moment, but he had to know. “Cas, I-” Dean started. “I know Dean,” said Cas. “Me too.” Dean nodded. They leaned their heads against each other and took a breath. Dean turned back around and let himself be held. He fell asleep soon after and didn't have any nightmares that night. When Dean awoke Cas was still holding him. He smiled.


End file.
